In his novel “To Have and Have Not,” Ernest Hemingway painted a compelling portrait of Depression-era Key West, his home in the 1930s. The 2026 Hemingway Look-Alike Contest and festival, scheduled Tuesday through Sunday, July 21-26, celebrates his influence on the island — highlighted by the Look-Alike Contest at Sloppy Joe’s Bar, 201 Duval St., and events that honor his writing talent.
The festival opens Tuesday, July 21, the 127th anniversary of the writer’s birth, with the announcement and reading of the Lorian Hemingway Short Story Competition’s winning entry. The literary challenge is directed by Hemingway’s granddaughter Lorian, also an author, and awards $2,500 annually to deserving writers.
The reading takes place at 6 p.m. at Williams Hall, 729 Fleming St., and is followed by a screening of “The Beard Also Rises.” The short film by Cassidy Rast and Odin Wadleigh celebrates the annual Hemingway Look-Alike Contest and its winners and entrants. Also planned is a “trailer” preview of the duo’s “Beards Go to Cuba,” showcasing the Look-Alikes’ philanthropic activities in support of the Cuban people.
At 8:15 that night, Williams Hall will show “The Old Man and the Sea,” the classic 1958 film based on Hemingway’s novella, “The Old Man and the Sea.” Spencer Tracy stars as Santiago, the Cuban fisherman who wages an epic battle with a giant marlin.
Cultural events continue Thursday, July 23, with an exploration of Hemingway’s love of Florida Keys angling and his lesser-known fisheries conservation activities. “Following the Fish: Hemingway in Key West” is presented by Cori Convertito, curator of the Key West Art & Historical Society. Part of her popular “Happy Hour with the Historian” series, it’s set from 5 to 6 p.m. at Comedy Key West, 218 Whitehead St.
A salute to Hemingway’s storytelling skill is planned Sunday, July 26 from 1 to 4 p.m. in an establishment that’s home to the award-winning Papa’s Pilar Rum. The “Papa’s Tales” Storytelling Competition will take place at the Hemingway Distillery’s Hemingway Social Club, 201 Simonton St. Entrants in two categories must spin a spoken-word tale of three minutes or less, with judges evaluating them on style, delivery and originality. Entry is free and the grand prize includes the Barrel Head Trophy.
The cultural schedule is bookended Tuesday and Sunday, July 21 and 26, by “Hemingway Collection” museum days at the Key West Museum of Art and History at the Custom House, 281 Front St. Attendees can view rare artifacts and memorabilia from the author’s life, a full-size bronze of him, and 59 original drawings by marine wildlife artist Guy Harvey illustrating “The Old Man and the Sea.” Admission is free to those who mention the Hemingway festivities upon arrival.
More information is at keywestlookalikes.com.
